Working Remotely, Part 1

I found that this post on Twitter had an unusual level of pickup and debate:

Is remote work more effective? Or is it less effective? Or is it about the same? As a person coming up on his first year anniversary working remotely at Automattic, that was a question that I asked at the beginning of this journey. But these days, and now a year in, I ask myself simply, “How do I become an effective executive leader remotely?”

By being an all-remote company of 500+ people across 50+ countries, Automattic has been the perfect place in which to learn from the best remote work culture on the planet. Operating across a 100% remote, flat, and transparent organizational landscape has posed many challenges for me this year. And I have loved every single one of them as opportunities to force myself to grow. I’ll touch upon how I’ve addressed each of them in future posts here. Thanks for being curious about remote working and creative leading!


In my experience, 100% remote for the whole company has lots of advantages. 50%-ish remote is probably the hardest for everyone. 10% remote is painful for the remote people but the “locals” can get by just fine. I’ve survived all of them, but only thrived in the 100% remote situations. Looking forward to your insights from the 100% world.

Yes that is what I have learned is an important factor — that when you have a part of the work force remote and a part of the work force non-remote, it creates two classes. And the remote folks can easily become the subclass. I can imagine cases where it could be vice-versa in the near future.